You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2013-07-22 19:49:31 UTC
Update Date2016-02-11 08:18:52 UTC
HMDB IDHMDB61126
Secondary Accession NumbersNone
Metabolite Identification
Common Name4,5-Dihydro-drospirenone-3-sulfate
Description4,5-Dihydro-drospirenone-3-sulfate is a metabolite of drospirenone. Drospirenone, also known as 1,2-dihydrospirorenone, is synthetic, steroidal progestin with additional antimineralocorticoid and weak antiandrogen properties which is used as a hormonal contraceptive. It is sold under the brand names Yasmin, Yasminelle, Yaz, Beyaz, Ocella, and Angeliq, all of which are combination products of drospirenone with an estrogen such as ethinylestradiol. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H34O5S
Average Molecular Weight434.589
Monoisotopic Molecular Weight434.212694888
IUPAC Name(2S,4R,10S,14S,16S,18S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolane]-7-sulfonic acid
Traditional Name(2S,4R,10S,14S,16S,18S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolane]-7-sulfonic acid
CAS Registry NumberNot Available
SMILES
C[C@]12CCC3C([C@H]4C[C@H]4C4CC(CC[C@]34C)S(O)(=O)=O)C1[C@@H]1C[C@@H]1C21CCC(=O)O1
InChI Identifier
InChI=1/C24H34O5S/c1-22-6-3-12(30(26,27)28)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(25)29-24/h12-18,20-21H,3-11H2,1-2H3,(H,26,27,28)/t12?,13-,14+,15-,16?,17?,18+,20?,21?,22-,23+,24?/s2
InChI KeyInChIKey=ZHIWICDXDMTIEM-TYRGJQATNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Oxolane
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015 mg/mLALOGPS
logP1.12ALOGPS
logP3.07ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)-0.73ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity110.4 m3·mol-1ChemAxon
Polarizability47.7 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00741
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB61126
Metagene LinkHMDB61126
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available